Tough Questions You Should Always Ask a Hiring Manager

Tough Questions You Should Always Ask a Hiring Manager
Photo: fizkes, Shutterstock

You’ve reached the end of a job interview, or maybe you’ve just been offered a new role. You’re feeling confident. Then, your potential future manager asks if you have any questions for them. How can you tactfully secure critical information about your future boss, directly from your future boss?

Now is the time to give yourself full permission to take on the role of interviewer. It’s not an easy task. You’re well-aware you’re still being judged for a position, but you also want to gain critical insight into your future boss’s values. Asking the right questions can help you both solidify a good impression and come to an informed decision about what it will be like to work with this person.

Below are some tough questions to ask your potential manager that will help reveal whether the work environment is the right one for you.

Can you please tell me a story that illustrates your management style?

Don’t expect to get a meaningful answer from asking someone “what’s your management style?” Think about when someone asks you the dreaded “What are your greatest strengths/weaknesses?” question. Rattling off a list of attributes isn’t reliable. Instead, the key is to get a story that actually demonstrates what you’re looking for. Hopefully, your future boss will be able to tell one about fostering the sort of work environment you’re seeking. If they can’t think of any examples that paint their management in a positive light, consider how that could impact your job.

How do you handle performance problems? Do you have a real-life example?

If the previous question didn’t provide much insight into your future manager’s style, this is a more specific approach. Does this person describe their process for giving constructive feedback? Does their tone hint at some suppressed rage? Of course, in any interview, you face the issue of an unreliable narrator. Hopefully, asking for a concrete example of your boss being, well, a boss will help you decide whether or not this seems like a desirable manager/employee relationship for you.

How did you approach the last promotion on your team?

The point of this question is to discover several things about your potential for growth down the line: how often promotions happen, what it takes to get them, and how your potential manager specifically contributes to them.

Again, asking how the promotion happened is crucial to getting a fuller picture of how the promotion process works on your future team. Plus, you want to make sure that you’re accepting a role where you’ll have the opportunity to grow with the team, if that’s what you want.

Is this a new position or are you hiring to replace someone?

Plus the follow-up: Why did the last person leave? This question is daunting, but could be revelatory. Pay attention to how comfortable your interviewer is answering this question, and listen for signs of a potentially toxic workplace. Is there an unusually high turnover rate? Or, on the other hand, was the last person promoted into a better role — forging a path you could see yourself following?

How will the arrival of your new hire make your job easier?

In addition to finding out how you can be a true asset, the answer here could also reveal what exactly your manager really expects from you. Hearing directly from a boss why your role is important will be more meaningful than a bunch of bullet points from the original job description.

All of my interviewers were men. Can I speak to some women on the team to hear more about their experience?

This question comes from Lily Konings, a product designer at Instagram. Konings writes that she picked it up from, “a candidate that specifically requested to speak to me, the only woman on the team at the time. (Spoiler: She accepted the offer after our call.)” If you’re going to committing to a new workplace, it’s helpful to hear from a diverse set of perspectives before you hop on board.

Final thoughts

Flipping the script to ask your interviewer questions can be intimidating for a lot of job seekers. However, it’s a crucial opportunity for both you and your potential employer. You’ll prove that you’re a critical thinker, and you’ll gain insight into whether or not this workplace seems right for you.

And no matter what, preparing questions for an interviewer is a must — failing to ask anything will make it seem as if you’re not fully invested or even interested in the position. If all goes well, hopefully your next question will be: So, when can I start?

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